April Underwood is the former Chief Product Officer at Slack. She was early at Twitter and made great friends at Google. As she describes in the podcast, the collection of people from companies A, B, and C is the foundation of one's network. April picked companies where she loved the product and knew these were people (Stewart Butterfield, Dick Costolo) she'd love building with. At this point in her career, April is an early-stage investor, co-founder of #ANGELS, and serves on the boards of Zillow and Eventbrite. In a fun conversation with Annie, hear April’s recommendations on building relationships, making good asks, and connecting friends.
April Underwood is the former Chief Product Officer at Slack. She was early at Twitter and made great friends at Google. As she describes in the podcast, the collection of people from companies A, B, and C is the foundation of one's network. April picked companies where she loved the product and knew these were people (Stewart Butterfield, Dick Costolo) she'd love building with. At this point in her career, April is an early-stage investor, co-founder of #ANGELS, and serves on the boards of Zillow and Eventbrite. In a fun conversation with Annie, hear April’s recommendations on building relationships, making good asks, and connecting friends.
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“Networking and mentorship oftentimes sounds like something that you can just go do. I think that you have to, in my experience, foster those relationships. You network and you cultivate mentors through both on the job experiences, but also like real personal connection. Those are where I think people can really show up for one another because they know, they know you and you know them.” - April Underwood
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Episode Timestamps:
*(03:50) - How April’s begnings as an intern at Deloitte Consulting as an intern lead to connections
*(05:31) - Why it’s important to foster work relationships outside of the workplace
*(07:52) - How April cultivated a relationship with Dick Costolo, former CEO of Twitter
*(09:29) - How April made smart choices throughout her career by joining, Google, Twitter, Slack
*(12:33) - Let your gut be your guide
*(14:57) - Choose the path where you feel at ease and feel like your best self
*(17:11) - How April created a relationship with Katie Jacobs Stanton
*(23:39) - Why relationships don't get built in a single meeting, but in multiple interactions
*(29:27) - The importance of #ANGELS
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Sponsor:
Who Got Me Here is brought to you by Connect The Dots, mapping professional relationships so you can find the strongest connections to the people and companies you want to reach. Visit ctd.ai to learn more.
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Links:
0:00:31.3 Annie Riley: Welcome to Who Got Me Here, a podcast about making connections matter. I'm your host, Annie Riley and today we are so lucky to be joined by April Underwood. April is a seasoned operator, investor, board member. She was an exec at high growth tech companies for over 20 years, having led teams in the early days of Google, Twitter, Slack, across product and partnerships, really interesting work experiences. In 2015, April co-founded #ANGELS with five colleagues from Twitter before angel groups were cool. And now April supports a growing portfolio of companies as an investor and serves on the boards of Zillow and Eventbrite in addition to getting into all sorts of interesting stuff. April, welcome to the show. We're so excited to have you.
0:01:18.1 April Underwood: Thanks so much for having me.
0:01:19.6 Annie Riley: I'm really excited to dig in but I guess before we kind of get into your experiences, when we talk about networking, a lot of times our guests have impressions of that word or associations with that. And I'm curious when we talk about networking, what comes up for you? What do you think about?
0:01:36.3 April Underwood: I go back to when I first probably started to be aware that that was even a term probably in college but perhaps my early 20s after college. And I had a sense that it was like something I was supposed to do. So one of the connotations I have with it is the sense of sort of obligation or the sense that it's exercise, brush your teeth and network. And I think we'll probably get into this but I think that that can lead to sort of approaching connecting with other people, which for me, it actually is about and it's sort of purist and also most valuable form. A lot of that happens, I think oftentimes more organically and it happens over a longer time period than I think people may want to hear. The best connections that I've made have happened relatively organically, although I did work to make those actually stick and to make those deeper and over time, both give and get value from those connections. So the connotation for me with networking is it feels a little cringy. It feels a little bit like trying to get people to spend time with you when there's not oftentimes a reason to.
0:02:37.4 April Underwood: And I think that there are some real ways that you can approach connecting with other people and also just like the mindset that has helped me find a way to do it that felt authentic rather than feeling like I was bugging people, which I think was probably true early on in my networking career.
0:02:52.7 Annie Riley: Yeah, totally. I guess I'd love to go back to the beginning because my understanding is that you started your career in engineering and you were able to make the transition into product. I'd love to hear about that transition and the role that relationships played in helping you to make that shift.
0:03:10.2 April Underwood: And actually, I'd love to even go back a half step earlier than that because I did not get a computer science degree in college. I got a business undergraduate degree in management information systems but I did a part-time job where I was doing tech support. And I realized that if I taught myself to code, I could get off the phones and I could start building the training modules for the rest of the folks at the call center. And I found that work sort of more rewarding. If I'd known about negotiation, I might have realized that also that was like a valuable time to consider renegotiating my compensation but I was making $10 an hour in Austin, Texas in 1998. I was like, this is amazing. So I was happy.
0:03:49.0 Annie Riley: Yeah, you struck gold.
0:03:50.6 April Underwood: Yeah, exactly. I didn't even know what I was missing out on. So I taught myself to code but I went through college, I had a number of internships. I wrote code in all of them. I took a few CS courses but I was not an obvious candidate for engineering roles after college. So I actually had to convince people to get into engineering, not to sort of go directly to product management. So that actually starts one of the first connections I made through my journey, which was when I was an intern at Deloitte Consulting in the summer of 2001, I was the only undergraduate intern on my project that I was assigned to. I begged to be put on an out of town project. And that out of town project meant that I ate breakfast, lunch and dinner with my team every day, Monday through Thursday for 10 weeks. And on that project was an MBA student who was naturally five, six years older than me, named Kara Whitehill. And so we started on this project together, we had this like formative experience over the summer together, sort of at different stages of our career. We had a lot of time outside of office and project work to get to know each other.
0:04:48.0 April Underwood: So when we went back to school in the fall, I think probably she did the work, frankly, to like stay in touch with me because I don't know that I had that bit yet but we probably met up once or twice that last year we were both finishing up school. And then when I went off to Oregon to go work for Intel after school as a software engineer, which it was a job I got through campus recruiting, I turned to her when I decided I wanted to go work on a consumer facing product. She had joined Travelocity in product. And so she opened that door for me. So you know, we had been on this internship together for this very short amount of time but that relationship, her vouching for me actually was how I was able to come in the door initially as a product management candidate but actually, I didn't know what product was. So I was like, no, I'm an engineer. And they were like, well, maybe. And so I did the interview and got the job. And no doubt because of not only her making the intro but her being able to vouch for my work.
0:05:41.1 April Underwood: So I'd say even those early experiences, there can be people around the table that can end up having a big impact on your career trajectory. And so one of the things that I've realized is that the deepest connections I've built in the workplace actually oftentimes really get fostered outside of the workplace. And that's something I've had to work at again and again in my career to make sure that I'm prioritizing that amongst all the other things I could do with my time outside the office.
0:06:05.5 Annie Riley: And when you were in those non-client moments together, I'm assuming you weren't just talking about the project.
0:06:12.7 April Underwood: No, not at all. I mean, we might have been having a laugh about access to the project... But one of the things I reflect upon from the first decade of my career is a lot of my socializing, it was at dinners, it was at happy hours. And I think now about a generation of folks that are coming out of college where a higher percentage of them are not necessarily looking... They're not that interested in drinking alcohol. They're looking for other ways and healthier ways, frankly, than the late '90s in terms of how to socialize and so I think there have to be new avenues for that but certainly in my experience, that was where a lot of the connectivity happened, because you're getting to know each other on a personal level. Obviously people's guards were down, you know, you're building real friendships with these people. So I think that working and mentorship oftentimes sounds like something that you can just go do but in my experience, you foster those relationships, you sort of cultivate your network and you cultivate mentors through both on the job experiences but also like real personal connection. Those are where I think people can really show up for one another because they know you and you know them.
0:07:14.2 Annie Riley: Yeah. And this is such a great example, because Cara, she wasn't the partner on the project. She was an MBA intern, a little bit ahead of you. And that's so great, I think, as an example, because a lot of times we look to sort of the most senior people and we say, okay, I want to be like that person. I want to get their time. I want to get their mentorship. And the connection that really, it sounds like launched your career came from someone who was a mentor and was a fellow intern on the project. And I think that's a really neat lesson for people that these relationships can be extremely beneficial across all levels in an organization.
0:07:51.8 April Underwood: That's right. And she was also the only other woman on this project. It was probably about an eight person project team. She was the only woman on the project. First of all, thank goodness she was there. That would have been a long summer as the only woman on that project. And we'll talk about some of the other folks. We'll talk about Dick Costolo, for example, former CEO of Twitter and an investor but I actually met him when we were both at Google together. And so over time, I've learned how to also cultivate those relationships with men and with people that don't look like me. And I think that that's an important skill set as well. I think I oftentimes always turned to women earlier in my career. And I think there's a lot of value in women networks and women mentorship. And we'll talk about #ANGELS and the role that that plays there but it's absolutely been beneficial for me to learn how to develop those relationships across the spectrum.
0:08:39.8 Annie Riley: One of the things I wanted to ask you about is how you have picked the companies that you've joined, because you have this great track record of joining winners, right? When you're joining a startup, especially when it's maybe 100, 150 employees, the stage that you joined places like Twitter and Slack, you don't necessarily know what's going to happen to the company. There's so much uncertainty. And I think now more than ever, people are thinking about joining places and they want to control the outcome or they want to pick something that's going to be good for their career and surround them with really smart, talented people who ultimately become their network. And I am curious how you have made these choices, these selections repeatedly throughout your career, Google, Twitter, Slack.
0:09:29.7 April Underwood: Well, so I'll start with Google because I feel like it's almost a little bit different. I got really lucky. I was in business school from 2005 to 2007. I actually thought I was going to leave tech and do something different. While I was there, a bunch of companies started launching what we started to call digital media. So these media companies that were starting to build experiences, YouTube came out while I was in school. Then the iPhone came out a few months after I interned at Apple. It was actually at the final stages of being ready to launch while I was on campus but I never would have known that because I was in a different bunker building that was not privileged enough to have that information. I got to see this unfold. And when I was in business school, the default thing to do with a business degree was management consulting at banking or perhaps commercial real estate. There were a bunch of CSRs. And I went to Haas at the University of California, Berkeley. And so there were a bunch of different amazing paths you could take with an MBA but there was a small group of people and we kind of considered ourselves like rebel MBAs or something because we wanted to go take our MBAs to work at places that had no obvious monetization model.
0:10:38.6 April Underwood: So you go to business school to learn how to run a business but if you go to a consumer company and they haven't figured out how to monetize yet, then you're really leaning on product design instincts and a sense for the core user problems that need to be solved and things like user behavior and research. It's sort of a skill set of things that frankly were not taught in the classroom then but an organization was started the year before I was in school called Digital Media and Entertainment Club, DMEC. And it was started by a bunch of guys now who've gone on to... One runs product at Aura now. One is very senior at YouTube. And some of them had built and sold companies to media outlets. Some of them worked with me at Twitter. So with Google, it was like Google is coming on campus. It was the hot ticket. I worked hard for the interviews and then went into Google. Google was already like 12,000 people. It was not small.
0:11:28.7 Annie Riley: Yeah. Different stage.
0:11:30.4 April Underwood: Yeah. I had a short stint there, I was there a few years, I learned a ton. I built an amazing network that, by the way, has paid off much more 10 years down the road than it necessarily was obvious that it would when I was there but that is what opened the door for me to join Twitter. So joining both Twitter and Slack, it's a very similar story. I had no idea those businesses were going to become what they've become. When I went to Twitter, I didn't even necessarily understand what that looked like because I'd never been through the real hypergrowth stage of a company of going from like 0 to $2 billion in revenue. I'd never seen that before. But by the time I got to Slack, I'd seen that before. I certainly thought that that opportunity was there but the thing that both had in common was I already loved the product before I walked in the door for the first conversation. It was a product that I could not get enough of. And so that was the real guide. And then when I walked in the door and I met the people, when I met the team at Twitter, when I first met with Stewart Butterfield, I knew that these were people that I would love building with, that I'd love spending the better part of my days with and that would make me better and that would energize me and that I wanted to be friends with.
0:12:33.3 April Underwood: So I really kind of let my gut be my guide in both of those. And one I'd say there's a big luck component in that but I think it was also an intuition that they had keyed in on something that wasn't just a business opportunity but they'd keyed in on something that was a cultural shift. For Twitter, that was a desire to express yourself publicly, like in what we later called the Global Town Square, to actually have a truly public, unadorned, unfiltered way to communicate with the world and all the amazing and turns out, also sometimes terrifying things that can unlock. And then on the Slack side, it was that people wanted to bring their whole selves to work, that they wanted to be able to work in communication tools that were as high quality and also as adaptable as what they had in their personal lives and that business software had not caught up to. So both of those, it was like, this is an amazing product, could be an amazing business but it was that cultural shift and just my love for the product and for the team that brought me there.
0:13:28.8 Annie Riley: And when you met the team, you mentioned this spark, this connection, people who you respected, wanted to be friends with. What was it that you saw in those people that made you feel compelled to join?
0:13:41.0 April Underwood: I mean, it was more checking in with myself of how I felt in those conversations. It felt really easy. You know, it didn't really feel like an interview. It felt like a conversation. And I found myself in the interviews really having a two-way dialogue with the people that I was talking to. You and I first interacted at class on campus at Stanford about humor. I laughed in probably all of those interviews. And for me, that is like a big sign. If there's that connection and comfort right off the bat where you're at ease and you know that people are having a good time and like finding humor in the situation, for me, that's like green lights all around. I don't think I've ever steered wrong when I follow that.
0:14:22.4 Annie Riley: So often I think we think about what are the qualities of the people we want to surround ourselves with? We want them to be X and Y and Z but I love this because you're not saying that they had any set of traits in common. It was how you felt when you were around them. And so that's such a great guide for thinking about who are the type of people you want to seek out? What are the relationships that you want to invest in? It's the ones that allow you to feel like you're at your best, allow you to feel comfortable, allow you to be laughing. And that kind of internal check, I think that's a really insightful lesson for people.
0:14:57.8 April Underwood: You can choose the path where you feel at ease and feel like your best self.
0:15:02.0 Annie Riley: It's probably a lot more fun to choose that path too.
0:15:04.9 April Underwood: Oh, absolutely. I mean, you feel grateful every day. And we're recording this in this moment where there's a lot of love being expressed amongst Twitter employees as things are really evolving for that company. I've always said, I think company cultures are a reflection of the products that they build. And so walked into Twitter and it was like a trading room floor. People were like shouting across the floor, hilarious, just like almost tears laughing almost every single day. Funniest collection and smartest and creative and original group of people I've ever been lucky enough to work with. And then when I walked into Slack, you could hear a pin drop because it was just for work and it was about being an effective team and people were typing in Slack rather than shouting across the floor at each other but still many of the same attributes. They were expressed in a different way but similarly hilarious and brilliant and really focused about values, really thoughtful about the impact of the things we were building. I don't know how to put it but people really gave a damn, not just about the business we were building but about the broader world and context that we live in.
0:16:10.3 April Underwood: So it's interesting and watching... What's been happening on Twitter for me has been really interesting to see some of the overlaps even between those two networks. Because I will say, especially in Silicon Valley but I think this is true in any industry, the network you build in one company extends into the next company and it opens the doors into the company after that. It's not like you have these distinct networks, it's a web. And so those relationships and the impressions that you make in your early jobs do stick around and that can be a really positive thing because they can mean that when you reconnect with people in a future life, as I have with a number of people, you're like, oh yeah, we were... Like, I knew you from Google for like a minute and now we're here at Twitter or we're here at Slack. Isn't this amazing? And have like sort of an immediate form of trust but I think that you do think about these networks not over months or even years but sometimes decades.
0:17:02.7 Annie Riley: Do you have an example of one or two of those relationships that have been part of that web for you and how they've helped you over time?
0:17:11.6 April Underwood: So one I'll mention because it's very, very concrete is Katie Jacobs Stanton, who's now one of my partners in #ANGELS that we've been building over the last seven years. She and I first met in 2009 at Google. I was working for a really great guy named Bill Brocker and I had been seeking out a mentor and so this is one of those instances where I really took action and I said I was looking for a mentor and he's like, I want you to meet this woman, Katie Jacobs Stanton. So I met her and I mean, she was just incredible clearly and she was working in new business development, she'd worked in product before, she'd been early at Yahoo. So she had this career that I was like just so in awe of and taking notes and wanting to figure out how I could build my own version of that. You know, we had one or two interactions and then she got pulled away to go work for the state department for Hillary. And so I was like, well, now I am even more fandom and sort of out of reach. She's like off in DC and she's doing that.
0:18:10.6 April Underwood: You know, it was kind of bittersweet. And then once I'd been at Twitter for about probably six months, in the door walks Katie Stanton to come be our VP of international. And so then we got the chance to work together for four or five years. Out of that came #ANGELS, which is this partnership among six of us that goes on forever but that all started with me asking for something, us having a couple of limited interactions but I think in both directions, there was enough there for both of us that when we landed in the same place again, that we sort of picked back up where we left off. And then our relationship has just evolved and blossomed into this amazing partnership.
0:18:48.0 Annie Riley: And you all, it sounds like hadn't even kept in close touch in those intervening years. Is that right?
0:18:52.8 April Underwood: I may have followed her probably like on Twitter, I suppose. I'm Facebook friends with her. She was somebody I'd met a couple of times. I was like, I was in awe of that and kind of figured our paths might not cross again but just a few years later, they did. Similarly, Dick Costolo, I mean, Dick Costolo, there's less of a gap there but Dick's company had been acquired by Google. I was a program manager working on acquiring all of the content that couldn't be crawled. So we would have all of these feeds of data from business listings or real estate listings or event listings or traffic data. And so all of that data had to come into the Borg and had to be scrubbed to make sure it was high quality. And so I was responsible for a team of people as well as some systems that we built to make all that possible.
0:19:39.8 April Underwood: But every time it came time to do OKRs or planning, I had a hard time attaching a business number to that. It's a hard thing. It was sort of complex and it got a little contrived at some point to sort of say, like, here's the impact dollar of all of these so I need 20% more headcount next year or whatever. And then Dick Costolo got up in front of an all hands for sort of an adjacent organization and talked about this vision for syndicating content across not just Google properties but really across the web and then add units into it. And so I was like, that's the solution. If only we can attach the advertising dollars that all of these efforts sort of drive, this solves a problem for me but also, I'm really excited about this vision. So I ran up to him afterwards. I was like, hey, I'm April. And we got to know each other a little bit but when he would come to visit Mountain View from Chicago, I would just basically calendar stalk him and be like, oh, looks like you're coming into town. Or when are you coming into town next? Can we get coffee? And so we just got coffee every few months for probably a year. And so then when he went off to be the COO of Twitter and another good friend, Isaac Hepworth joined from Google to Twitter and pinged me to come over, then I had that warm connection to Dick.
0:20:48.7 April Underwood: And obviously, it grew to much more than that as we actually had the opportunity to truly work together over the next five years but it all started with I had a need and he looked like the white knight from product to come show up with something that would be helpful in my day to day, in my planning and growing. And then again, we had built a personal connection.
0:21:10.8 Annie Riley: Can we talk more about how you actually translated that into a personal connection? Because what you just described is something that I think a lot of people would love to do but maybe it feels too hard or they don't want to impose and they kind of end up chickening out. That whole process of walking up to Dick, introducing yourself and inserting yourself into his world, how did you navigate that? Did some of those fears and worries come up for you? And tactically, what did you do to make that a real relationship?
0:21:42.2 April Underwood: It started from the realization that he was doing something that was valuable to me but also I was doing something that was likely going to be valuable to him. And I think that you can't manufacture that. One of the things I think is valuable before you meet somebody is to not only do your homework and just understand more about them so that you can try to find some points of connection but if you can find some ability to just start some conversation that goes sort of outside of the very, very tactical or transactional, I should say, I think that's valuable but the transactional piece is also important. You need to come to these opportunities both thinking about what you would like to get and what you may have to offer. And when you're very early in your career, you may think you don't have anything to offer. I've been there but I will say also early in your career, you may not actually know what you want from the person. And I think that oftentimes leads to the most sort of like disappointing, like one and done, you're probably not going to have an interaction with that person again.
0:22:39.8 April Underwood: So even if it feels like a stretch, I do think it's better for you to try to think about something that you can offer that could be valuable and also something specific and concrete that you think that person can help you with that's not a huge ask. The transactions are almost like the fuel on the spark that can start to like build a real connection. The conversation is probably good dating advice too but I would just say you kind of have to show interest in what they're interested in. And so I think that sometimes you show up and people are just not really as open to that. And I'd say that's just hard. If they're putting out some opportunity for you to connect with them personally, I think that... Sometimes when you're young, you might feel nervous and you might feel like you need to rush it along. And I think sometimes you may leave a meeting and you're like, we didn't talk about anything I thought we were going to talk about but I feel like I know that person so I feel more comfortable sending them the next email or the next text. So yeah, thinking of these relationships as things that don't get built in a single meeting but in multiple interactions takes the pressure off to some degree.
0:23:40.1 Annie Riley: Yeah. Super helpful for relieving the pressure and it's just helpful to think about being present in the conversation. It can be really easy to get in your own head and kind of give a lot of attention to that talk track running in the background. And this idea of just being present, taking their lead and seeing where the conversation goes, I think is really helpful advice. Just thinking about this idea of like being really specific in the ask and being present in the conversation. Now you're in the position of being someone who a lot of people would love to get time with. What does a good ask for you look like? So if someone is reaching out to you wanting to build that connection, what does it look like to ask for something specific in the way that you're recommending?
0:24:19.9 April Underwood: It's a few things. So you've done your homework, you know a bit about who this person is. You likely already had some sort of an interaction too, because I think you're typically trying to avoid leading with an ask but it could be the first outbound, you're trying to get that first coffee with them. And so you're trying to show that they might have an enjoyable 30 minutes if they chat with you. And also that there is something specific that they can do for you that will be meaningful for you. I think the elements are... It's specific. I think that another thing that I have done to try to develop these relationships is be open to an alternative solution that they may provide. So I have at different points in my career, not even necessarily by design but I have connected other people and then their relationship has long outlasted or gone much deeper than the relationship I had with either one of them. And so that's another form of a plan B you can offer, which is you probably have a ton of constraints on your time but if there's anybody on your team that might be able to help me understand a little bit more about what a path to an internship might look like, I'd be really grateful.
0:25:31.0 April Underwood: That just makes it very easy. When you ask people for something that's big and concrete, if the answer is no, it is oftentimes easier not to reply but if you give somebody these soft no paths, maybe there'll be something next year or here's a PM on my team that loves meeting up and coming product managers, then it just makes it really easy for them. So I would just almost think through the eyes of the receiver of how do you make this a decision tree that is very easy for them to take some action on rather than none. Like that's the goal.
0:26:03.5 Annie Riley: This idea of a graceful plan B is one that I'm definitely adding to the toolkit. Can we talk about #ANGELS and how you decided to get that started with that particular group of five women?
0:26:18.3 April Underwood: Yeah. Well, so even before #ANGELS, one of the things that I did at Twitter was at some point I realized I was the most senior woman in product. I was in like a meeting and it was 12 directors and all the other ones were men. And so I realized, gosh, it's on me. Like how did this happen? I definitely would not have been that person at Google. There were many women more senior than me. At Twitter, we were a much smaller, earlier company. And so I started this group and basically I think I went to some exec, maybe it was Dick or somebody else. I was like, I'm going to take all the women product managers to dinner and you're going to pay for it. And they're like, great. So that's something that you can almost always do. Obviously budget constraints being what they are maybe in this particular moment but oftentimes people are pretty happy if you take the initiative to create those networks inside your company. And I think company based networks are the foundation of one's network. It's the collection of people you worked with at company A, B and C. And then those start to cross over and then they start to get richer and then you start to reach outside of the companies you've worked at as you get deeper into your career.
0:27:17.5 April Underwood: So with #ANGELS, I was the most senior woman in the product organization. The other five women were also the most senior women in their part of the organization, meaning their peer team, they were likely the only woman in the room. And so we all knew each other sometimes because we'd actually done some work together and other instances, it was more social. We all had an interest in angel investing and we felt like we needed to get the word out that we're available here to write checks because we saw a lot of our male peers after the Twitter IPO getting to invest in the next cohort of great companies and we wanted to participate in that. And so we put on a medium post, we said, we're #ANGELS, we're here, one of us invests, you get six for the price of one in terms of like help and expertise. And we wrote our own checks and immediately got a really amazing response. And that response was a lot of other women that were like, Hey, I want to angel invest or can I join #ANGELS? It was just, there was so much appetite to join something like this.
0:28:16.2 April Underwood: And since then there've been a number of different alumni syndicates that have come out of some really great companies and oftentimes they call us to ask us, how does it work? As they're getting it started. It's just awesome to see because it's a great model and it's a great way to extend those relationships you've built inside a company to like be very meaningful and real for many years after you all leave the company because we text each other a bunch every single day and we haven't all worked together in seven years, which is pretty incredible. So the thing that we did with that though, is we started holding events. Similar to the Twitter women's story, we realized that a lot of the venture capital firms wanted to get to know more amazing senior women operators. And so we started holding events, not just for women, sometimes it was a mix like some of our portfolio founders but we started holding these events and we've done like 25 of them over the years up until the pandemic. And then hopefully we'll get back to those soon as people seem pretty eager to reconnect but those connections started to foster, they were networking opportunities for the people that participated and for us, it was just sort of extending our good fortune to have a network where we could call up the VCs, the folks we knew over there and ask them to host these great events.
0:29:27.1 Annie Riley: That's awesome. Yeah. And so the events were for other female operators kind of interested getting involved in angel investing, not necessarily for seeking investment. Am I getting that right?
0:29:37.9 April Underwood: It was a mix. Mostly it was pretty senior operators because you could wind the clock back to 2015, there were very few women in these roles and we were all kind of looking to like find each other and be able to have some conversation over dinner. And kind of like the one on one thing I talked about, maybe the preamble that we got up and gave at the beginning was about angel investing or about the gap table when we did the first study that showed that only 9% of the nominal value of equity in all of Carta's companies that was owned by women. And then they've done great work to extend that further into like a bunch of additional dimensions including race as well as also extending it to non-binary. So like they've done a bunch of really great work since then but we kind of got the ball rolling by just asserting that it was true without the data. And then fortunately they showed up with the data to back us up, which was great. So we might've started our event talking about that but I will tell you the conversation at the table would lead to egg freezing frequently.
0:30:38.7 April Underwood: That was a common topic or to other aspects of people's lives that of course had implications for their work but they mostly were like a good time but amongst a really incredible set of people who've gone on to have those connections. And so some of those going all the way back to Google through both #ANGELS, as well as my role as a chief product officer at Slack, I've gotten to reconnect with and go to conferences with some of the women who were very senior when I was at Google. It was not... I was earlier in my career, I was straight out of business school but like Stacy Brown-Philpot or Kim Scott, these women that were VP level-ish when they were at Google had become friends because when I bumped into them at a conference in 2019 or 2018 when I was running product at Slack, we knew we had that connection and it just gave us this point to jump off from. And so just starting with that peer cohort and then knowing that in time people's roles are going to grow and evolve and you're going to have all sorts of ways to be helpful to one another as you go along your career.
0:31:40.8 Annie Riley: Okay. I'd love to chat with you about the role that relationships played in your board service and your board appointments. Board service is something a lot of folks, especially as they get more senior strive for. I hear a lot of people asking, what are the things I have to do to get on a board? What type of experiences should I get now to set myself up? But I'd imagine that relationships also are huge for this and we'd love to hear more about the role that relationships have played in both getting onto these boards and also being a successful board member.
0:32:13.1 April Underwood: They absolutely do play a role. And I think that I have benefited from that and I also recognize that this is why [0:32:21.1] ____ work around board lists, Brad Gerstner has specifically done some work around getting women of color onto boards. So there's a number of really amazing people that are well positioned to help facilitate these connections. For me personally, I got invited to an amazing event that was a small sort of weekend event with a handful of people across the tech industry, the venture world. One of those folks there was Rich Barton, who's now the CEO of Zillow but when I joined the Zillow Group board, he was actually the chairman of the board and there was another person acting as CEO. And I'm sure he talked to a ton of people but that was where we had that connection. And then I went through a process and interviewed for the role and got it. Similarly, I recently joined Eventbrite. Julia Hartz and I have known each other because at some point when you're a senior woman in a not women dominated field like tech, then you run into a lot of the same people over and over again but we didn't know each other well.
0:33:19.0 April Underwood: And she was looking for a technical board member and reached out to me. And so we spent some time talking about it and beginning to know our team but in both cases, we were known quantities to one another as we had that exploration. And I would say I think that is very, very common. And so while I do get recruited for board seats and get emails from executive recruiters and I will say I oftentimes don't dig into those because on both sides of that relationship, the question is why? Why do you want to be on that board and why do they want you on that board? You think about a board, it is most often literally a room of people that spend time together four times a year, maybe more but other than that, only in the most intense times for that company. There's a completely understandable desire for the chairman as well as for the CEO to have folks in the room that they think are going to bring a lot of value but also that you're not necessarily looking to add like a wild card to that situation because again, you're only going to really be relying on your board in some of the most challenging moments or decisions for the company.
0:34:25.1 April Underwood: So it's understandable, it does create some challenges. The good news about board work is I think there was this big push a few years ago and frankly when I joined this little group where there was a sense of like, all women need to get on boards. I also have come to realize that board work is something that you can do into your 60s and 70s. You can do like for a long period and also in later chapters of your career. Nobody needs to be like in a rush to go do that because there's plenty of time to do that but I would say that starting to cultivate those relationships with people that might end up being CEOs or that also that are going to be on boards themselves ends up oftentimes, at least in this day and age being the vector by which you at least get the conversation and then it's up to you to deliver in those interviews.
0:35:08.0 Annie Riley: Yeah, it goes back to what you were saying earlier about playing the long game and investing in those relationships over time. So then you're a known entity and you have that relationship when they are looking for that board member.
0:35:21.2 April Underwood: That's right. That's right. But I started in Amarillo, Texas. I didn't know anything about companies even. I had no exposure to anything related to this industry, to business. I showed up to college not even knowing what business was. So I have an incredible amount of privilege and access that I've accrued over time and I'm very, very aware of it. And hopefully the encouraging thing that I can share is that I built all of with no obvious on ramps towards this and have sort of worked my way there and also have met some really wonderful people along the way because I've been open to people and building those relationships and that has made all the difference.
0:36:02.1 Annie Riley: Amazing. Well, April, I could talk to you all day. You have such an amazing story and you bring so much warmth and energy to the conversation. So it's such a pleasure to have you on. Thank you, April, for sharing all of your insights and experiences with us. It's been a pleasure, a joy to have you on.
0:36:19.0 April Underwood: My pleasure. My pleasure.